Fluorescent probe with functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activity as well as preparation method and application thereof

A fluorescent probe and photodynamic technology, applied in photodynamic therapy, chemical instruments and methods, fluorescence/phosphorescence, etc., can solve the problems of no photodynamic killing cancer cell activity, limited application range, etc., and achieve strong light resistance Bleaching ability, reducing background interference, avoiding the effect of self-absorption

Active Publication Date: 2020-01-03
INNER MONGOLIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, a few AIE molecules used to detect hydrogen peroxide have been reported in the literature, but there are very few AIE molecules that can detect hydrogen peroxide in lipid droplets in real time, and the existing AIE molecules for detecting hydrogen peroxide do not have photodynamic killing of cancer cells. The scope of application restricted

Method used

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  • Fluorescent probe with functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activity as well as preparation method and application thereof
  • Fluorescent probe with functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activity as well as preparation method and application thereof
  • Fluorescent probe with functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activity as well as preparation method and application thereof

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preparation example Construction

[0048] The present invention also provides a method for preparing the fluorescent probe described in the above technical solution, comprising the following steps:

[0049] (1) the compound with structure shown in formula II, 4-(bromomethyl) phenylboronic acid and the first organic solvent are mixed to carry out salt-forming reaction, to obtain the compound with structure shown in formula III;

[0050]

[0051] Wherein, in formula II and formula III, R is hydrogen, alkyl, alkoxy, N,N-dimethyl, N,N-diethyl or N,N-diphenyl;

[0052] (2) Mixing the compound having the structure shown in formula III with malononitrile, an organic base and a second organic solvent, and performing Knoevenagel reaction under a protective atmosphere to obtain a fluorescent probe having the structure shown in formula I.

[0053] In the present invention, the compound having the structure shown in formula II, 4-(bromomethyl) phenylboronic acid and the first organic solvent are mixed to carry out salt-...

Embodiment 1

[0075] The following formula 1 shows the chemical reaction formula of this embodiment to prepare a fluorescent probe with both hydrogen peroxide detection and photodynamic killing activity of cancer cells:

[0076]

[0077] (1) Compound 1 (497.6 mg, 1.00 mmol), 4-(bromomethyl)phenylboronic acid (257.8 mg, 1.20 mmol) and toluene were mixed, refluxed at 130° C. under the protection of nitrogen, and the reaction progress was monitored with a TLC plate Until compound 1 disappears completely, complete the salt-forming reaction; then cool to room temperature, add anhydrous diethyl ether to the obtained reaction solution, let stand for 30min, wherein the volume ratio of the reaction solution and anhydrous diethyl ether is 1:3, then suction filtration to obtain Solid 370.5 mg, the calculated yield is 52%;

[0078] The obtained solid was characterized by NMR and the results are as follows:

[0079] 1 H NMR (400MHz, DMSO-d 6 )δ9.34(d,J=6.3Hz,2H),8.32(d,J=6.2Hz,2H),8.18(s,2H),7.85(...

Embodiment 2

[0117] Substitute compound 1 with the compound represented by the following formula II-2, and other conditions are the same as those in Example 1,

[0118]

[0119] The obtained product was characterized by NMR, and it was known that the obtained probe was the compound shown in I-2.

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Abstract

The invention provides a fluorescent probe with functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activity as well as a preparation method and application thereof, and belongs to the technical field of a biochemical material. The fluorescent probe with the functions of detecting hydrogen peroxide and performing photodynamic killing on cancer cell activityhas aggregation induced luminescence characteristic, can specifically respond to the hydrogen peroxide, generates a substance with stronger fluorescence, can be applied to detection on the hydrogen peroxide in cells, and can selectively position subcellular organelle lipid droplets in the cells; the product obtained through action between the fluorescent probe and the hydrogen peroxide has large stokes displacement, so self-absorption can be avoided and background interference can be reduced; the fluorescent probe as well as the product obtained through the action between the fluorescent probeand the hydrogen peroxide have high light stability and photobleaching resistance, and are suitable for long-time tracing of the hydrogen peroxide in living cells or living bodies; meanwhile, the product obtained through the action between the fluorescent probe and the hydrogen peroxide has active oxygen generation capacity, can be applied to photodynamic killing of the cancer cells and can construct a diagnosis and treatment reagent integrating diagnosis and treatment functions.

Description

technical field [0001] The invention relates to the technical field of biochemical materials, in particular to a fluorescent probe with both hydrogen peroxide detection and photodynamic killing activity of cancer cells, and a preparation method and application thereof. Background technique [0002] Hydrogen peroxide (H 2 O 2 ) is one of the important members of the reactive oxygen species family (Reactive Oxygen Species, ROS), which plays a key role in the physiology, pathology and cell signaling of living organisms. More and more literature reports have confirmed that the abnormal content of hydrogen peroxide in the body is closely related to a variety of diseases, such as stroke, diabetes, arthritis, cardiovascular disease and tumors. In particular, tumor hypoxia will induce tumor cells to produce more hydrogen peroxide and lipid droplets. Therefore, the development of a rapid, sensitive, real-time online detection method for endogenous hydrogen peroxide in intracellular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K41/00A61P35/00
CPCC07F5/025C09K11/06A61K41/0057A61P35/00G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1014G01N2021/6439G01N2021/6443G01N2021/6417
Inventor 王建国姜国玉刘祥
Owner INNER MONGOLIA UNIVERSITY
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